3-Methyl-4H-chromen-4-one.

In the title chromenone derivative, C(10)H(8)O(2), the two fused six-membered rings are coplanar, with a mean deviation of 0.0261 (1) Å from the plane through the non-H atoms of the rings. The carbonyl and methyl substituents of the pyran ring also lie close to that plane, with the O and C atoms deviating by 0.0557 (1) and 0.1405 (1) Å, respectively. In the crystal, weak C-H⋯O contacts form chains along the a axis.

Related literature

For the pharmaceutical applications of chromanone compounds, see: Shi et al. (2004 ▶). For related structures, see: Takikawa & Suzuki (2007 ▶); Patonay et al. (2002 ▶); Alaniz & Rovis, (2005 ▶).

Experimental

Crystal data

C10H8O2

M = 160.16

Triclinic,

a = 6.5284 (13) Å

b = 7.2210 (14) Å

c = 8.9834 (18) Å

α = 75.137 (2)°

β = 78.169 (2)°

γ = 80.895 (2)°

V = 398.12 (14) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.12 × 0.10 × 0.08 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.989, T max = 0.993

2771 measured reflections

1394 independent reflections

1143 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.116

S = 1.00

1394 reflections

111 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.14 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810020453/sj5009sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810020453/sj5009Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C10H8O2	Z = 2
Mr = 160.16	F(000) = 168
Triclinic, P1	Dx = 1.336 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.5284 (13) Å	Cell parameters from 1573 reflections
b = 7.2210 (14) Å	θ = 2.4–28.4°
c = 8.9834 (18) Å	µ = 0.09 mm−1
α = 75.137 (2)°	T = 296 K
β = 78.169 (2)°	Block, colorless
γ = 80.895 (2)°	0.12 × 0.10 × 0.08 mm
V = 398.12 (14) Å3

Bruker APEXII CCD diffractometer	1394 independent reflections
Radiation source: fine-focus sealed tube	1143 reflections with I > 2σ(I)
graphite	Rint = 0.014
φ and ω scans	θmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −7→7
Tmin = 0.989, Tmax = 0.993	k = −8→8
2771 measured reflections	l = −10→10

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039	H-atom parameters constrained
wR(F2) = 0.116	w = 1/[σ2(Fo2) + (0.065P)2 + 0.067P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
1394 reflections	Δρmax = 0.18 e Å−3
111 parameters	Δρmin = −0.13 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.032 (10)

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
C1	0.5883 (2)	0.71757 (18)	1.05339 (16)	0.0417 (3)
C2	0.4277 (2)	0.76708 (17)	0.96592 (15)	0.0390 (3)
C3	0.4728 (2)	0.76636 (18)	0.79936 (15)	0.0427 (4)
C4	0.6928 (2)	0.71855 (19)	0.73797 (16)	0.0455 (4)
C5	0.8332 (2)	0.6710 (2)	0.83389 (17)	0.0503 (4)
H5	0.9726	0.6398	0.7905	0.060*
C6	0.7581 (3)	0.7246 (3)	0.56727 (18)	0.0700 (5)
H6A	0.9074	0.6903	0.5445	0.105*
H6B	0.7222	0.8524	0.5078	0.105*
H6C	0.6864	0.6350	0.5400	0.105*
C7	0.2263 (2)	0.8210 (2)	1.04176 (18)	0.0506 (4)
H7	0.1150	0.8533	0.9864	0.061*
C8	0.1897 (3)	0.8271 (2)	1.19601 (19)	0.0602 (4)
H8	0.0549	0.8646	1.2443	0.072*
C9	0.3541 (3)	0.7771 (2)	1.28035 (18)	0.0607 (5)
H9	0.3291	0.7818	1.3851	0.073*
C10	0.5524 (3)	0.7212 (2)	1.21027 (17)	0.0554 (4)
H10	0.6621	0.6859	1.2671	0.066*
O1	0.33452 (17)	0.80490 (17)	0.71782 (12)	0.0648 (4)
O2	0.79069 (14)	0.66418 (15)	0.98916 (11)	0.0522 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0424 (7)	0.0398 (7)	0.0441 (7)	−0.0053 (5)	−0.0089 (6)	−0.0103 (5)
C2	0.0379 (7)	0.0336 (6)	0.0444 (7)	−0.0056 (5)	−0.0078 (5)	−0.0057 (5)
C3	0.0444 (8)	0.0392 (7)	0.0440 (7)	−0.0064 (6)	−0.0133 (6)	−0.0031 (5)
C4	0.0487 (8)	0.0439 (7)	0.0421 (7)	−0.0055 (6)	−0.0062 (6)	−0.0080 (6)
C5	0.0397 (8)	0.0574 (9)	0.0522 (8)	−0.0016 (6)	−0.0028 (6)	−0.0162 (7)
C6	0.0782 (12)	0.0787 (12)	0.0445 (9)	−0.0009 (9)	−0.0016 (8)	−0.0108 (8)
C7	0.0418 (8)	0.0482 (8)	0.0594 (9)	−0.0046 (6)	−0.0063 (6)	−0.0106 (6)
C8	0.0552 (9)	0.0551 (9)	0.0635 (10)	−0.0085 (7)	0.0104 (7)	−0.0168 (7)
C9	0.0803 (12)	0.0573 (9)	0.0437 (8)	−0.0141 (8)	0.0018 (8)	−0.0164 (7)
C10	0.0673 (10)	0.0573 (9)	0.0461 (8)	−0.0084 (7)	−0.0180 (7)	−0.0129 (7)
O1	0.0559 (7)	0.0849 (8)	0.0544 (7)	−0.0039 (6)	−0.0253 (5)	−0.0076 (5)
O2	0.0403 (6)	0.0681 (7)	0.0517 (6)	0.0017 (5)	−0.0162 (4)	−0.0184 (5)

C1—O2	1.3668 (17)	C6—H6A	0.9600
C1—C2	1.3854 (19)	C6—H6B	0.9600
C1—C10	1.387 (2)	C6—H6C	0.9600
C2—C7	1.3967 (19)	C7—C8	1.368 (2)
C2—C3	1.4657 (19)	C7—H7	0.9300
C3—O1	1.2312 (16)	C8—C9	1.388 (2)
C3—C4	1.450 (2)	C8—H8	0.9300
C4—C5	1.332 (2)	C9—C10	1.366 (2)
C4—C6	1.4961 (19)	C9—H9	0.9300
C5—O2	1.3548 (17)	C10—H10	0.9300
C5—H5	0.9300
O2—C1—C2	121.70 (12)	H6A—C6—H6B	109.5
O2—C1—C10	116.53 (12)	C4—C6—H6C	109.5
C2—C1—C10	121.77 (14)	H6A—C6—H6C	109.5
C1—C2—C7	117.46 (13)	H6B—C6—H6C	109.5
C1—C2—C3	120.18 (13)	C8—C7—C2	121.23 (14)
C7—C2—C3	122.34 (13)	C8—C7—H7	119.4
O1—C3—C4	122.69 (13)	C2—C7—H7	119.4
O1—C3—C2	122.50 (13)	C7—C8—C9	119.91 (15)
C4—C3—C2	114.81 (11)	C7—C8—H8	120.0
C5—C4—C3	119.62 (13)	C9—C8—H8	120.0
C5—C4—C6	121.16 (14)	C10—C9—C8	120.34 (14)
C3—C4—C6	119.22 (13)	C10—C9—H9	119.8
C4—C5—O2	125.65 (13)	C8—C9—H9	119.8
C4—C5—H5	117.2	C9—C10—C1	119.28 (14)
O2—C5—H5	117.2	C9—C10—H10	120.4
C4—C6—H6A	109.5	C1—C10—H10	120.4
C4—C6—H6B	109.5	C5—O2—C1	117.89 (11)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1i	0.93	2.70	3.4374 (19)	137
C7—H7···O2ii	0.93	2.69	3.3820 (19)	132

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1i	0.93	2.70	3.4374 (19)	137
C7—H7⋯O2ii	0.93	2.69	3.3820 (19)	132

Symmetry codes: (i) ; (ii) .